Two-Week Italy Self-Drive Road Trip With Itinerary from Milan to Como, Verona, Venice, Florence, Siena, and Rome

Day 2 of your road trip across Italy promises a magnificent time exploring Milan. You have 1 night left in Milan. Take the opportunity to experience more of the best attractions and activities in the city.

Make sure to visit Navigli, a popular neighborhood in Milan. Spend some time wandering around the area and soak in its distinctive charm. You’ll also discover that several of the city’s must-see attractions are just around the corner.

Bring your curiosity for today’s adventure around Milan. Some of the city’s most loved attractions await! Duomo Di Milano Museum is the perfect place to start. This church is one of the most world-famous places to visit in Milan. Next, head to Galleria Vittorio Emanuele Ii, a famous shopping mall, known for its romantic features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Sforzesco Castle Art Library. This historic castle is a highly recommended experience. Nearby, you'll also find Parco Sempione and Piazza Gae Aulenti. Visit these for an interesting touch to your journey.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

As you explore more of Milan, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.

Treat yourself to a wonderful meal at Dessert Bar Milano, a top-rated dining spot in Milan. If you're in the mood for something new, try Radisson Blu Hotel Milan, another premier location with a delectable menu. You might also want to book a table at Ristorante Qui Si Mangia. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Milan.

After enjoying a fulfilling meal, continue your evening at Kilburn Cocktail Bar Milano, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Bar Frida offers a welcoming atmosphere for easing into the nightlife. Similarly, The Friends Pub Milano provides an excellent environment for a relaxed and enjoyable evening.

Raise your glass and celebrate another amazing day of your road trip in Italy!

Embark on another extraordinary experience on day 3 of your road trip in Italy. Today, you will make 4 stops and experience some of the highlights of Como, Rogaro, Lenno, and Colonno. At the end of the day, you will enjoy the comforts of a top-rated hotel in Como, which will be your home away from home for 1 night.

Start your day with a visit to Basilica Di San Fedele. This intriguing church is a must-visit in the city. When you’re ready for your next discovery, continue to Saint Mary Assunta Cathedral, which may be one of the most history-steeped places you will experience today.

One of the best things about exploring Milan on a self-guided tour is that you set the pace. There’s plenty of time for detours and discovering hidden gems. When you’re ready for your next stop, make your way to Villa Carlotta (lake Como), an often recommended museum in the city. If you’re up for more discoveries, don’t forget to reserve some time for Villa Del Balbianello and Greenway Del Lago Di Como.

When you’re done exploring for the day, you’ll drive to your hotel in Como. Check in and spend some time relaxing before you head out to tour the city.

Indulge in a memorable dining experience at one of Como's most popular restaurants, and connect with friendly locals for an authentic adventure.

Treat yourself to a delicious dinner at L’Antica Trattoria, an excellent option for tonight's dining. Looking for something different? Gesumin Restaurant offers a tantalizing alternative with its diverse menu. And don’t miss Pronobis. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Como.

After savoring a delicious meal, step into the vibrant nightlife at Fresco Cocktail Shop, where the evening is just getting started. In the same way, Bar Il Cortiletto offers a unique charm perfect for experiencing the local bar scene in Como. Bar Pinocchio is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Get a good night's sleep and look forward to another great day on the road in Italy!

On day 4 of your road trip in Italy, you will get a true taste of the freedom a self-drive vacation in Europe entails. Today’s travel plans include stops at the most scenic, wondrous, and interesting places in Verona. In the evening, you’ll end up in Verona, where you will stay for 1 night.

Today's adventure in Como promises more breathtaking discoveries and enriching experiences! Begin at Giusti Garden. This mesmerizing botanical garden is a highlight of any visit in the city. Then, enjoy Ponte Pietra, another history-steeped attraction that never fails to captivate visitors. Next, head over to Piazza Dei Signori, one of the city’s most locally appreciated attractions, known for its romantic features.

If you’re looking for more, spend time soaking in the atmosphere of Piazza Delle Erbe. This romantic public square is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Castelvecchio Museum, a captivating museum, and take a stroll around the area. If you want to extend your self-guided sightseeing tour, go check out Verona Arena before you head back to your hotel.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Verona. Verona offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

As dinnertime approaches, it's time to head out for a bite to eat in Verona. If you are looking to dine at a popular restaurant in the city, it's often a good idea to reserve a table in advance.

Have a fantastic dining experience at La Griglia, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Vecio Macello offers an enticing alternative with its varied menu. Additionally, Via Fama Cafè | Verona is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Verona.

Cap off your dinner by heading to Archivio, ideal for a leisurely evening with a drink in hand. La Segreteria Café is another bar that offers an enjoyable setting. Similarly, Grande Giove Cocktail Bar is also a popular place to go on a night out, perfect for relaxing and socializing.

Head back to your accommodation in Verona and get some rest in preparation for another magical day of your road trip in Italy!

Dive into day 5 of your remarkable road trip in Italy. Today you will explore Venice, where you will have the opportunity to experience all the top things to see and do. At the end of the day, you’ll unwind at one of the finest accommodations in Venice. You’ll stay here for 2 nights.

Today’s route brings fun adventures, romantic experiences, and breathtaking views. The first attraction of today is Santa Maria Della Salute. This curiosity-inducing church is a romantic place to see in Verona. Continue your discovery at Peggy Guggenheim Collection, a history-steeped art gallery with stories to tell.

As you stroll around Verona, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Santa Maria Gloriosa Dei Frari. This intriguing church offers a breathtaking encounter with Verona. Next, make your way to Grand Canal to add another highlight to your day. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Verona.

At the end of the day, you will drive to Venice, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

After a day of adventure, treat yourself to an exquisite dinner at one of Venice's best restaurants.

Don’t miss out on dining at Bauer Hotel, a top-rated dining destination in Venice. If you're in the mood to try something new, consider L'Osteria Le Guglie, another top spot with a mouthwatering menu. You might also want to secure a reservation at Corner Pub. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Venice this evening.

Round off your dining experience by visiting Al Parlamento, a prime location for a drink. Alternatively, explore the distinctive characteristics of The Caffe Rosso, a bar catering to every mood and preference. Adagio likewise offers a unique atmosphere, perfect for a memorable night out.

Raise your glass to another unforgettable day in Italy!

On day 6 of your road trip, you will have an entire day to explore Venice. You’ll stay in Venice for 1 night and discover all the best things to see and do in the area.

Today, you'll explore some of the most beautiful places in Venice, including a historical landmark, an opera house, a public square, a church, a palace, a monument and much more! Start your day with a visit to Rialto Bridge. This iconic historical landmark is a must-visit in the city. When you’re ready for your next discovery, continue to Teatro La Fenice, which may be one of the most romantic places you will experience today.

One of the best things about exploring Venice on a self-guided tour is that you set the pace. There’s plenty of time for detours and discovering hidden gems. When you’re ready for your next stop, make your way to Piazza San Marco, a world-famous public square in the city. If you’re up for more discoveries, don’t forget to reserve some time for St Mark's Basilica and Doge's Palace. End your day with a visit to Bridge Of Sighs, a notable monument that’s sure to leave a lasting impression.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Venice. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Have a fantastic dining experience at Generator Venice, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Nevodi offers an enticing alternative with its varied menu. Additionally, Ristorante La Piazza is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Venice.

Following your dinner, dive into the local bar culture at Il Mercante. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to The Irish Pub Venezia, the perfect place for those looking to experience the best of the nightlife. Similarly, Ai Stagneri provides excellent drinks and a great atmosphere, ensuring a memorable night out.

Raise your glass to another unforgettable day in Italy!

On day 7 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Florence. When you’re not sightseeing, take time to relax at your selected hotel in Florence, where you’ll be staying for 3 nights.

Venice is home to plenty of attractions that offer family-friendly attractions, romantic experiences, and breathtaking views! Start at Piazzale Michelangelo, a spectacular observation deck that is worthwhile a visit in the city. Nearby, you’ll find Basilica Of Santa Croce In Florence, enchanting visitors with its culturally significant appeal. Continue your exploration at David. This statue is one of the city’s most interesting spots.

Enjoy the freedom of exploring Venice at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Central Market. After exploring the food market, head to the widely recognized Cathedral Of Santa Maria Del Fiore.

When you’re done exploring for the day, you’ll drive to your hotel in Florence. Check in and spend some time relaxing before you head out to tour the city.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Florence. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Treat yourself to a wonderful meal at Ristorante Oliviero 1962, a top-rated dining spot in Florence. If you're in the mood for something new, try Di Poneta Novoli, another premier location with a delectable menu. You might also want to book a table at Caffe San Firenze. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Florence.

If you’re not ready to end the night just yet, Manifattura offers a perfect venue to relax and savor a drink. Similarly, Se·sto On Arno Rooftop Bar is well-suited for those looking to unwind in a social setting. Il Vinile is another excellent spot to enjoy a nightcap after a delightful meal.

Celebrate another amazing day of your road trip adventure in Italy!

Day 8 offers a multitude of experiences. You will stay in Florence for 2 nights more, offering you enough time to explore at a relaxed pace.

One of the most iconic places you can visit today in Florence is Oltrarno. Allow yourself some time to explore this neighborhood and discover its unique quirks. You'll also find many of the best sightseeing spots nearby.

Today’s well-planned self-sightseeing route offers several family-friendly attractions, romantic experiences, and scenic views. Whether you decide to explore Florence on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Ponte Vecchio is the first of them. Spend some time admiring this symbolic historical landmark before continuing your journey. Piazza Della Signoria is your next stop. This impressive public square is one of the best-rated sights in Florence.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Bargello National Museum. This photogenic museum is a sight to behold. To round off your sightseeing experience, visit Palazzo Vecchio and Uffizi Gallery.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

Indulge in a memorable dining experience at one of Florence's most popular restaurants, and connect with friendly locals for an authentic adventure.

Treat yourself to a delightful dinner at Ditta Artigianale, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Trattoria Da Burde? It's another excellent option with a diverse menu. Consider reserving a table at Casa Toscana as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Florence.

To truly maximize your evening out, consider visiting Bar 50 Rosso after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Bitter Bar, another bar with an inviting ambiance. Similarly, Archea Brewery also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

Relax and reminisce about your day in Italy and look forward to more memorable moments to come!

On day 9 of your road trip, you’ll start and end your day in Florence, where you'll stay for 1 night more.

Get ready to discover some of the most iconic wonders in Florence, including a church, a public square, a monument, a cemetery and much more! Start your day at Santa Maria Della Spina. This culturally significant church is an underrated place to see in Florence. Then, wander over to Knights' Square. If picture-perfect sites excite you, this public square will be right up your alley. Nearby, you’ll also find Leaning Tower Of Pisa. This masterful monument is a favorite among visitors.

Florence offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Pisa Cathedral is an intriguing spot in the city that will captivate you with its unique charm. When you’re done at the church, don’t forget to check out the grand Piazza Del Duomo, Pisa. Take a moment to appreciate the fascinating details of this iconic public square. Wrap up your self-guided tour of Florence's top attractions with a visit to Campo Santo.

When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Florence.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Florence. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Enjoy a lovely dining experience at Ristorante Buca Mario, a popular restaurant in Florence. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Florence at Agricola Toscana, another great place to eat. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. A third option to check out is the top-rated Eataly Firenze. It’s yet another ideal choice to enhance your time in Florence tonight.

Let the evening flow smoothly from dinner to drinks at Gosh*, a top-rated bar in the area. For other recommendations, Antico Caffè Del Moro - Art Bar Firenze provides a perfect setting for rounding out your night with style and great drinks. Likewise, Quelo Bar offers a memorable night with diverse drink options and excellent service.

Raise your glass to another unforgettable day in Italy!

Experience an unparalleled adventure on day 10 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Siena. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Siena. You will spend 1 night here for some well-deserved relaxation.

Today’s well-planned self-sightseeing route offers several family-friendly attractions, breathtaking views, and picturesque spots. Whether you decide to explore Florence on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Porta Romana is the first of them. Spend some time admiring this culturally significant monument before continuing your journey. Palazzo Salimbeni is your next stop. This worthwhile palace is one of the best-rated sights in Florence.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Basilica Of San Domenico. This picture-perfect church is a sight to behold. To round off your sightseeing experience, visit Siena Cathedral and Pubblico Palace. If time allows, end your day with Piazza Del Campo, an UNESCO world heritage-listed public square that offers a memorable conclusion to your exploration.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Siena. Siena offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Siena. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Enjoy a delicious meal at Enoteca I Terzi, a highly-rated dining destination in Siena. If you're eager to try something different, consider Ristorante Tar-Tufo, another top spot with a tantalizing menu. You might also want to secure a reservation at Antica Trattoria Papei. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Siena this evening.

Continue the enjoyment post-dinner at Meet Life Cafè, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Maudit Pub offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Bar Impero Siena. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

As the sun sets on another day of adventure, rest up and recharge for the next leg of your road trip in Italy.

Embark on another extraordinary experience on day 11 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Rome. At the end of the day, you will enjoy the comforts of a top-rated hotel in Rome, which will be your home away from home for 3 nights.

Get ready to discover some of the most iconic wonders in Siena, including an archeological site, a public square, and a museum. Start your day at Colosseum. This historic archeological site is a timeless place to see in Siena. Then, wander over to Roman Forum. If historic sites excite you, this archeological site will be right up your alley. Nearby, you’ll also find Piazza Del Popolo. This masterful public square is a favorite among visitors.

Siena offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Capitoline Museums is a notable spot in the city that will captivate you with its unique charm.

At the end of the day, you will drive to Rome, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

As you explore more of Rome, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.

Make sure to reserve a table at La Bottega Roma, an iconic dining spot in Rome. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Pasta In Corso, a popular restaurant in Rome. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Trattoria Vecchia Roma, a hidden gem nestled in Rome. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Continue your lively evening at La Botticella Of Poggi Giovanni, a perfect place for winding down or revving up the night, depending on which mood you’re in. Almalu Trastevere is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Bar Viminale Di Pepi Maurilio ensures a night out tailored to your taste.

Take some time to reflect on your day and savor another beautiful night in Italy.

Wake up to day 12 of your extraordinary road trip in Italy. With 2 nights left in Rome, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Trastevere is a fantastic place you can explore today in Vatican City. This neighborhood is a testament to the city’s character, and it's easy to spend hours just walking around and admiring the surroundings. Soak in the Vatican City-way-of-life and visit all the nearby sights.

Start your adventure at Vatican Museums. This wondrous art museum is a place that is appreciated by travelers and locals alike.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to St. Peter's Basilica. This globally renowned major basilica offers an enriching experience. For a change of pace, head to Campo De' Fiori, where you can take in romantic features. Conclude your self-guided sightseeing tour with a visit to Piazza Navona. These sights offer a fulfilling end to a perfect day.

When you’re done exploring for the day, you’ll return to Rome and your accommodation.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Rome. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Make sure to reserve a table at RomAntica, an iconic dining spot in Rome. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Coso Ristorante, a popular restaurant in Rome. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of DEROMA - Farine Romane, a hidden gem nestled in Rome. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Keep the evening going at Sant' Eustachio Caffè, a great choice for enjoying the after-dinner hours with a drink. You could also go to Yellowsquare Rome, which offers a similarly pleasant setting and great drinks. Another option is Caffè Portofino, which provides an inviting environment for unwinding after a busy day out.

Head back to your accommodation in Rome and get some rest in preparation for another magical day of your road trip in Italy!

Day 13 of your road trip will take you to the best attractions Rome has to offer. Cherish the 1 night you have left in Rome by discovering the best things there are to see and do in the city.

Today’s agenda in Rome includes a church, a public square, a monument, a castle and much more! Basilica Of San Clemente is must-visit church and a great starting point for the day. Next, continue your journey to Spanish Steps, an impressive public square, located just a leisurely stroll away. Next, head to Piazza Di Spagna, a history-steeped public square, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Rome. When you're ready, let your sightseeing route take you to the wondrous Trevi Fountain. If you’re looking for more, Pantheon is also an iconic attraction that is worthwhile a visit. Lastly, don’t miss Castel Sant'angelo, a place of history-steeped interest in the city.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

As dinnertime approaches, it's time to head out for a bite to eat in Rome. If you are looking to dine at a popular restaurant in the city, it's often a good idea to reserve a table in advance.

Enjoy a lovely meal at Hotel de Russie, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, La Taverna Italiana is another top choice with a popular menu. You could also check for a table at The Parrot Bar. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Rome tonight.

After your delicious meal, get a taste of the vibrant nightlife with a visit to The Apartment Bar Roma, known for its inviting atmosphere. Hotel Hassler Roma is another great option if you’re looking for a place to get the night started.

Savor another day of unforgettable experiences in Italy!

On day 14 of your road trip in Italy, you will get a true taste of the freedom a self-drive vacation in Europe entails. Today’s travel plans include stops at the most scenic, wondrous, and interesting places in Bologna. In the evening, you’ll end up in Milan, where you will stay for 1 night.

Set out on a day brimming with family-friendly attractions, breathtaking views, and photo-friendly spots. Start at the worthwhile Bologna Cathedral, a culturally significant church in Rome. Next, go to Piazza Maggiore.

After visiting Bologna Cathedral and Piazza Maggiore, have a stroll along Rome's streets and take in the local charm. Continue your sightseeing by heading to Two Towers. This respected monument offers a unique experience. Porta Maggiore is another noteworthy attraction worthwhile a visit.

When you’re done exploring for the day, you’ll drive to your hotel in Milan. Check in and spend some time relaxing before you head out to tour the city.

Indulge in a memorable dining experience at one of Milan's most popular restaurants, and connect with friendly locals for an authentic adventure.

Enjoy a delicious meal at Bice Restaurant, a top-rated dining destination in Milan. If you're in the mood to try something new, consider Alto Ristorante, another top spot with a mouthwatering menu. You might also want to secure a reservation at Nero 9. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Milan this evening.

After enjoying a fulfilling meal, continue your evening at Bhangrabar, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Rufus Cocktail Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Ostello Bello Grande provides an excellent environment for a relaxed and enjoyable evening.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in in Italy.